Aryl formamide compound and preparation method, pharmaceutical composition and application thereof

A technology for aryl formamides and compounds, applied in the field of aryl formamide compounds and their preparation, to achieve the effects of inhibiting aggregation, inhibiting the generation of VEGF, and inhibiting migration

Active Publication Date: 2019-11-05
ANHUI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current clinical anti-tumor drugs are mainly cytotoxic drugs, which inhibit cell growth. There is a lack of drugs on the market that use HIF-1 as a drug target to inhibit tumor metastasis, so as to prevent and treat metastatic malignant tumors and diseases related to pathological growth of retinal blood vessels.

Method used

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  • Aryl formamide compound and preparation method, pharmaceutical composition and application thereof
  • Aryl formamide compound and preparation method, pharmaceutical composition and application thereof
  • Aryl formamide compound and preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Synthesis of N-(2-chlorophenethyl)-2-methyl-thiazole-4-carboxamide

[0042] The reaction formula is as follows:

[0043] The synthesis steps are as follows:

[0044] (1) Dissolve 2-methylthiazole-4-carboxylic acid (1mmol) in 5mL of dichloromethane solution at 0°C, slowly add oxalyl chloride (0.17mL) and N,N-dimethylformaldehyde Amide (1 drop), add and react at room temperature for 1 hour, and after the reaction is completed, the solvent is distilled off under reduced pressure to obtain a residue;

[0045] (2) Dissolve the residue in 2 mL of dichloromethane, add 2-(2-chlorophenyl)ethylamine (1 mmol), dichloromethane (5 mL) and triethylamine (0.16 mL) into a mixed solution, and stir at room temperature 24h. After the completion of the reaction was confirmed by TLC analysis, the solvent was distilled off under reduced pressure, and the residue was purified by flash column chromatography to obtain the target compound as a colorless oil with a yield of 84.3%.

...

Embodiment 2

[0047] Example 2 Synthesis of N-(2-chlorophenethyl)-5-methyl-furan-2-carboxamide

[0048] Choose 5-methylfuran-2-carboxylic acid as the raw material, and other embodiments are the same as in Example 1.

[0049] The prepared compound was a colorless oil with a yield of 67.0%.

[0050] 1 HNMR (600MHz, CDCl 3 )δ7.37(dd, J=7.5, 1.5Hz, 1H), 7.28-7.26(m, 1H), 7.22-7.17(m, 2H), 6.99(d, J=3.3Hz, 1H), 6.37(brs , 1H), 6.08(d, J=3.3Hz, 1H), 3.68(td, J=7.0Hz, 2H), 3.05(t, J=7.0Hz, 2H), 2.32(s, 3H); 13 CNMR (151MHz, CDCl 3 )δ158.59, 154.32, 146.38, 136.51, 134.13, 131.00, 129.59, 128.02, 126.96, 115.28, 108.43, 38.77, 33.62, 13.74; ESI-HRMS (m / z) calcdC 14 h 14 ClNO 2 (M+H + ) 264.0786, found 264.0789.

Embodiment 3

[0051] Example 3 Synthesis of N-(2-chlorophenethyl)-2-(pyridin-3-yl)-thiazole-4-carboxamide

[0052] Select 2-(pyridin-3-yl)-thiazole-4-carboxylic acid as the raw material, and other embodiments are the same as in Example 1.

[0053] The prepared compound was a white solid with a yield of 74.1%.

[0054] 1 HNMR (600MHz, CDCl 3 )δ9.16(s, 1H), 8.70(d, J=5.4Hz, 1H), 8.19(d, J=7.8Hz, 1H), 8.15(s, 1H), 7.42-7.38(m, 2H), 7.30(dJ=7.8Hz, 1H), 7.24-7.19(m, 2H), 3.77(t, J=7.0Hz, 2H), 3.12(t, J=7.0Hz, 2H); 13 C NMR (151MHz, CDCl 3 )δ164.08, 160.22, 150.72, 150.65, 147.08, 135.84, 133.59, 133.11, 130.43, 129.08, 128.26, 127.55, 126.39, 123.16, 122.88, 38.54, 32.90; 17 h 14 ClN 3 OS(M+H + )344.0619, found344.0618.

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Abstract

The invention relates to the field of medicinal chemistry and pharmacotherapeutics, particularly discloses an aryl formamide compound and a preparation method thereof, and also relates to applicationof the compound in preparing drugs for preventing or treating diseases caused by upregulation of hypoxia-inducible factors, application of the compound in preparing drugs for preventing or treating tumors or retinal vascular diseases and a pharmaceutical composition containing the compound.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and pharmacotherapeutics, and in particular relates to an aryl formamide compound and its preparation method, pharmaceutical composition and application. Background technique [0002] Tumor metastasis is the primary cause of clinical tumor treatment failure and patient death. About 90% of cancer patients die not from the primary tumor but from tumor metastasis. Therefore, inhibition of tumor metastasis is a serious challenge for cancer therapy. Aiming at the key targets in the process of tumor cell invasion and metastasis, the research and development of effective drugs to inhibit tumor metastasis has become a new direction in the research and development of anti-tumor drugs, which has very important theoretical research significance and clinical application prospects. [0003] Diseases related to pathological growth of retinal vessels, including retinopathy of prematurity, diabetic r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C07D405/04C07D213/81C07D277/56C07D417/04C07D271/10C07D263/34C07D271/06C07D213/82C07D239/28C07D307/68C07D413/12C07D417/12C07D401/12C07D401/04C07D213/38C07C233/65A61P35/00A61P27/02A61P9/12A61P9/10A61P35/04A61K31/4436A61K31/443A61K31/4418A61K31/4439A61K31/4245A61K31/426A61K31/421A61K31/505A61K31/341A61K31/506
CPCA61P9/10A61P9/12A61P27/02A61P35/00A61P35/04C07C233/65C07D213/38C07D213/81C07D213/82C07D239/28C07D263/34C07D271/06C07D271/10C07D277/56C07D307/68C07D401/04C07D401/12C07D405/04C07D409/04C07D413/12C07D417/04C07D417/12
Inventor 刘明明王洋刘新华梁玉茹朱仲珍李荣石静波
Owner ANHUI MEDICAL UNIV
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